Within the synthetic new quinolone antibacterial agents, quinolone derivatives containing a 1,2-cis-2-fluorocyclopropyl group as a substituent at the 1-position have a strong antibacterial activity and are highly safe at the same time, and thus expected to be an excellent synthetic antibacterial agent. To prepare such 1,2-cis-2-fluorocyclopropyl group, 1,2-cis-2-fluorocyclopropane-1-carboxylic acid is useful. This compound is produced by dechlorinating 1-chloro-2-fluorocyclopropane-1-carboxylic acid ester in dimethyl sulfoxide in the presence of sodium borohydride (Japanese Patent Application Laid-Open No. 6-157418). However, this dechlorination reaction has a problem that when a stirring blade is used in the stirring step with the view of industrial production, it takes several days to complete the reaction, and therefore establishment of a convenient production method with a reduced reaction time has been desired. In addition, since dimethyl sulfoxide generates dimethyl sulfide which is responsible for foul odor during the reaction, there has been a problem of harmful effects on the environment.
Under such circumstances, an object of the present invention is to provide a method of producing 2-fluorocyclopropane-1-carboxylic acid ester by efficiently dehalogenating 1-halogeno-2-fluorocyclopropane-1-carboxylic acid ester, which method is also applicable to apparatuses for industrial production.